Acyclic 1,4-stereocontrol via reductive 1,3-transpositions
by Qi, Wei; McIntosh, Matthias C.
One-pot reduction/allylic diazene rearrangement of lactic acid- and mandelic acid-derived alpha,beta-unsaturated tosyl hydrazones leads to 1,4-syn- or 1,4-anti-E-2-alkenyl arrays in high yield and diastereoselectivity. Either the syn or the anti diastereomer can be prepared by choosing the appropriate alkene stereoisomer of the hydrazone. The E-alkenes led to the 1,4-syn isomers, while the Z-alkenes led to the 1,4-anti isomers, both with >= 20:1 diastereoselectivity.
- Journal
- Organic Letters
- Volume
- 10
- Issue
- 2
- Year
- 2008
- Start Page
- 357-359
- URL
- https://dx.doi.org/10.1021/ol702921x
- ISBN/ISSN
- 1523-7052; 1523-7060
- DOI
- 10.1021/ol702921x